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Chemistry

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Also known as: 21256-18-8, Daypro, 3-(4,5-diphenyl-1,3-oxazol-2-yl)propanoic acid, Alvo, 3-(4,5-diphenyloxazol-2-yl)propanoic acid, Oxaprozine

Molecular Formula

C₁₈H₁₅NO₃

Molecular Weight

293.3 g/mol

InChI Key

OFPXSFXSNFPTHF-UHFFFAOYSA-N

FDA UNII

MHJ80W9LRB

An oxazole-propionic acid derivative, cyclooxygenase inhibitor, and non-steroidal anti-inflammatory drug that is used in the treatment of pain and inflammation associated with of OSTEOARTHRITIS; RHEUMATOID ARTHRITIS; and ARTHRITIS, JUVENILE.

Oxaprozin is a Nonsteroidal Anti-inflammatory Drug. The mechanism of action of oxaprozin is as a Cyclooxygenase Inhibitor.

1 2D Structure

Oxaprozin

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

3-(4,5-diphenyl-1,3-oxazol-2-yl)propanoic acid

2.1.2 InChI

InChI=1S/C18H15NO3/c20-16(21)12-11-15-19-17(13-7-3-1-4-8-13)18(22-15)14-9-5-2-6-10-14/h1-10H,11-12H2,(H,20,21)

2.1.3 InChI Key

OFPXSFXSNFPTHF-UHFFFAOYSA-N

2.1.4 Canonical SMILES

C1=CC=C(C=C1)C2=C(OC(=N2)CCC(=O)O)C3=CC=CC=C3

2.2 Other Identifiers

2.2.1 UNII

MHJ80W9LRB

2.3 Synonyms

2.3.1 MeSH Synonyms

1. 4,5 Diphenyl 2 Oxazolepropionic Acid

2. 4,5-diphenyl-2-oxazolepropionic Acid

3. Apo Oxaprozin

4. Apo-oxaprozin

5. Danoprox

6. Daypro

7. Dayrun

8. Rhoxal Oxaprozin

9. Rhoxal-oxaprozin

10. Wy 21,743

11. Wy-21,743

2.3.2 Depositor-Supplied Synonyms

1. 21256-18-8

2. Daypro

3. 3-(4,5-diphenyl-1,3-oxazol-2-yl)propanoic Acid

4. Alvo

5. 3-(4,5-diphenyloxazol-2-yl)propanoic Acid

6. Oxaprozine

7. Oxaprozinum

8. Deflam

9. Wy-21,743

10. Oxaprozine [inn-french]

11. Oxaprozinum [inn-latin]

12. Wy-21743

13. Oxaprozina [inn-spanish]

14. Oxaprozina

15. 4,5-diphenyl-2-oxazolepropanoic Acid

16. 4,5-diphenyl-2-oxazolepropionic Acid

17. 2-oxazolepropanoic Acid, 4,5-diphenyl-

18. Duraprox

19. Oxaprozinum;wy21743

20. Wy 21743

21. Mfcd00215977

22. Nsc310839

23. Nsc-310839

24. 3-(4,5-diphenyl-2-oxazolyl)propenoic Acid

25. 3-(diphenyl-1,3-oxazol-2-yl)propanoic Acid

26. Beta-(4,5-diphenyloxazol-2-yl)propionic Acid

27. Mhj80w9lrb

28. Nsc 310839

29. Chembl1071

30. Chebi:7822

31. Voir

32. 2-oxazolepropionic Acid, 4,5-diphenyl-

33. .beta.-(4,5-diphenyloxazol-2-yl)propionic Acid

34. Danoprox

35. Dayrun

36. 3-(4,5-diphenyl-2-oxazolyl)propanoic Acid

37. Cas-21256-18-8

38. Dsstox_cid_25118

39. Dsstox_rid_80684

40. Dsstox_gsid_45118

41. Actirin

42. Xopane

43. Smr000058286

44. Daypro (tn)

45. Sr-01000076053

46. Oxaprosin

47. Durapro

48. Duraprost

49. Oxaprozi

50. Oxapro

51. Walix

52. Oxaprozin, Solid

53. Oxaprozin,(s)

54. Oxaprozin- Bio-x

55. Einecs 244-296-1

56. Nci310839

57. 4, 5-diphenyl-2-oxazolepropionic Acid

58. Brn 1083168

59. Oxaprozin [inn]

60. Oxaprozin [jan]

61. Oxaprozin [mi]

62. Oxaprozin [hsdb]

63. Oxaprozin [usan]

64. Maybridge1_008800

65. Prestwick0_001060

66. Prestwick1_001060

67. Prestwick2_001060

68. Prestwick3_001060

69. Spectrum2_001696

70. Spectrum3_001078

71. Spectrum4_001231

72. Unii-mhj80w9lrb

73. Lopac-o-9637

74. Oxaprozin [vandf]

75. Oxaprozin [mart.]

76. O 9637

77. Oxaprozin [usp-rs]

78. Oxaprozin [who-dd]

79. Schembl3286

80. Ncistruc1_000799

81. Ncistruc2_000787

82. Bidd:pxr0149

83. Lopac0_000944

84. Oprea1_509470

85. Bspbio_001020

86. Bspbio_002696

87. Kbiogr_001722

88. Mls000759535

89. Mls001424072

90. Bidd:gt0438

91. Spectrum1505267

92. Spbio_001652

93. Spbio_002940

94. Oxaprozin (jp17/usp/inn)

95. Bpbio1_001122

96. Gtpl7252

97. Oxaprozin [orange Book]

98. Dtxsid1045118

99. Hms566h22

100. Hsdb 7586

101. Kbio3_001916

102. Oxaprozin [usp Monograph]

103. Hms1571c22

104. Hms1922p17

105. Hms2051l15

106. Hms2093o08

107. Hms2098c22

108. Hms3262n10

109. Hms3393l15

110. Hms3652h17

111. Hms3715c22

112. Hms3885l11

113. Pharmakon1600-01505267

114. Wy21743

115. Amy32551

116. Bcp28431

117. Hy-b0808

118. Tox21_110059

119. Tox21_500944

120. 2-oxazolepropanoic Acid,5-diphenyl-

121. 2-oxazolepropionic Acid,5-diphenyl-

122. Bdbm50002861

123. Ccg-36508

124. Ncgc00014711

125. Nsc758949

126. S4230

127. Zinc49643479

128. 4,5-diphenyloxazole-2-propanoic Acid

129. Oxaprozin 100 Microg/ml In Methanol

130. 4,5-diphenyloxazole-2-propionic Acid

131. Akos000206807

132. Oxaprozin [usan:usp:inn:ban:jan]

133. Tox21_110059_1

134. Cs-7975

135. Db00991

136. Ks-5196

137. Lp00944

138. Nc00214

139. Nsc-758949

140. Sdccgsbi-0050918.p004

141. Ncgc00014711-01

142. Ncgc00014711-02

143. Ncgc00014711-03

144. Ncgc00014711-04

145. Ncgc00014711-05

146. Ncgc00014711-06

147. Ncgc00014711-07

148. Ncgc00014711-08

149. Ncgc00014711-09

150. Ncgc00014711-10

151. Ncgc00014711-11

152. Ncgc00014711-14

153. Ncgc00014711-15

154. Ncgc00094249-01

155. Ncgc00094249-02

156. Ncgc00094249-03

157. Ncgc00094249-04

158. Ncgc00094249-05

159. Ncgc00094249-06

160. Ncgc00094249-07

161. Ncgc00261629-01

162. Oxaprozin 100 Microg/ml In Acetonitrile

163. Ac-26512

164. Bo164184

165. Nci60_002681

166. Sy050819

167. Sbi-0050918.p002

168. 3-(4,5-diphenyl-2-oxazolyl)propionic Acid

169. Ab00514024

170. B1804

171. Eu-0100944

172. Ft-0638104

173. O0377

174. Sw197319-4

175. 3-(4, 5-diphenyl-2-oxazolyl)propenoic Acid

176. En300-25629

177. 3-(4,5-diphenyl-oxazol-2-yl)-propionic Acid

178. C07356

179. D00463

180. Ab00514024_08

181. Ab00514024_09

182. 256o188

183. A815225

184. 1-aminocyclobutane-cis-1,3-dicarboxylicacid

185. J-013955

186. Q1749609

187. Sr-01000076053-1

188. Sr-01000076053-3

189. Sr-01000076053-7

190. Sr-01000076053-9

191. 3-(4,5-diphenyl-1,3-oxazol-2-yl)propanoic Acid #

192. Brd-k25394294-001-05-7

193. Brd-k25394294-001-08-1

194. Z217102860

195. Oxaprozin, United States Pharmacopeia (usp) Reference Standard

2.4 Create Date

2005-03-25

3 Chemical and Physical Properties

Molecular Formula	C₁₈H₁₅NO₃
Molecular Weight	293.3 g/mol
XLogP3	4.2
Hydrogen Bond Donor Count	1
Hydrogen Bond Acceptor Count	4
Rotatable Bond Count	5
Exact Mass	293.10519334 g/mol
Monoisotopic Mass	293.10519334 g/mol
Topological Polar Surface Area	63.3 Å²
Heavy Atom Count	22
Formal Charge	0
Complexity	361
Isotope Atom Count	0
Defined Atom Stereocenter Count	0
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

4 Drug and Medication Information

4.1 Drug Information

1 of 4
Drug Name	Daypro
PubMed Health	Oxaprozin (By mouth)
Drug Classes	Analgesic, Antirheumatic, Central Nervous System Agent, Musculoskeletal Agent
Drug Label	DAYPRO (oxaprozin) is a nonsteroidal anti-inflammatory drug (NSAID), chemically designated as 4,5-diphenyl-2-oxazole-propionic acid, and has the following chemical structure:The empirical formula for oxaprozin is C18H15NO3, and the molecular weight i...
Active Ingredient	Oxaprozin
Dosage Form	Tablet
Route	Oral
Strength	600mg
Market Status	Prescription
Company	Gd Searle

2 of 4
Drug Name	Oxaprozin
PubMed Health	Oxaprozin (By mouth)
Drug Classes	Analgesic, Antirheumatic, Central Nervous System Agent, Musculoskeletal Agent
Drug Label	Oxaprozin, USP is a nonsteroidal anti-inflammatory drug (NSAID), chemically designated as 4,5-diphenyl-2-oxazole-propionic acid, and has the following chemical structure:The empirical formula for oxaprozin, USP is C18H15NO3, and the molecular weight...
Active Ingredient	Oxaprozin
Dosage Form	Tablet
Route	Oral
Strength	600mg
Market Status	Prescription
Company	Teva; Apotex; Sun Pharm Inds; Sandoz; Ivax Sub Teva Pharms; Dr Reddys Labs

3 of 4
Drug Name	Daypro
PubMed Health	Oxaprozin (By mouth)
Drug Classes	Analgesic, Antirheumatic, Central Nervous System Agent, Musculoskeletal Agent
Drug Label	DAYPRO (oxaprozin) is a nonsteroidal anti-inflammatory drug (NSAID), chemically designated as 4,5-diphenyl-2-oxazole-propionic acid, and has the following chemical structure:The empirical formula for oxaprozin is C18H15NO3, and the molecular weight i...
Active Ingredient	Oxaprozin
Dosage Form	Tablet
Route	Oral
Strength	600mg
Market Status	Prescription
Company	Gd Searle

4 of 4
Drug Name	Oxaprozin
PubMed Health	Oxaprozin (By mouth)
Drug Classes	Analgesic, Antirheumatic, Central Nervous System Agent, Musculoskeletal Agent
Drug Label	Oxaprozin, USP is a nonsteroidal anti-inflammatory drug (NSAID), chemically designated as 4,5-diphenyl-2-oxazole-propionic acid, and has the following chemical structure:The empirical formula for oxaprozin, USP is C18H15NO3, and the molecular weight...
Active Ingredient	Oxaprozin
Dosage Form	Tablet
Route	Oral
Strength	600mg
Market Status	Prescription
Company	Teva; Apotex; Sun Pharm Inds; Sandoz; Ivax Sub Teva Pharms; Dr Reddys Labs

4.2 Therapeutic Uses

Oxaprozin ... /is/ indicated for the treatment of acute or chronic rheumatoid arthritis. /Included in US product labeling/

Thomson/Micromedex. Drug Information for the Health Care Professional. Volume 1, Greenwood Village, CO. 2007., p. 376

Oxaprozin ... /is/ indicated for relief of acute or chronic osteoarthritis. /Included in US product labeling/

Thomson/Micromedex. Drug Information for the Health Care Professional. Volume 1, Greenwood Village, CO. 2007., p. 376

... In this open, multicenter, randomized, controlled study, eligible patients with periarthritis of the shoulder were randomized to receive either oxaprozin 1200 mg once daily (n = 49) or diclofenac 50 mg three times daily (n = 47). The treatment period was 15 +/- 1 days. The study was planned on a hypothesis of equivalence between the two study drugs. The primary study endpoint was the change from baseline at day 15 in the patient-assessed shoulder pain score. Secondary efficacy variables included investigator-assessed shoulder function, patient-assessed quality of life on the Short-Form-36 (SF-36) Acute Health Survey and both patients' and investigators' overall assessment of efficacy. At day 15, the mean changes in shoulder pain score from baseline in the oxaprozin and diclofenac groups were -5.85 +/- SD 4.62 and -5.54 +/- SD 4.41, respectively. The difference between the two groups was not statistically significant, confirming the hypothesis of the study that oxaprozin is as effective as diclofenac. Investigator-assessed shoulder function improved in both groups but more so in the oxaprozin group (p = 0.028 at day 15). Quality of life as measured by SF-36 total score was also improved in both treatment groups, with a trend toward greater improvement in the oxaprozin group. Furthermore, a significantly more favorable effect on the SF-36 'mental health' item was observed in oxaprozin compared with diclofenac-treated patients at day 15 (p = 0.0202). As assessed by investigators, the overall efficacy of oxaprozin was superior to that for diclofenac at visit 3 (8 +/- 1 days) (p = 0.0067). Patients also assessed the overall efficacy of oxaprozin as superior to that of diclofenac at visits 3 (8 +/- 1 days) (p = 0.0235) and 4 (15 +/- 1 days) (p = 0.0272). Only six adverse events, all of which were mild or moderate in intensity and occurred in four diclofenac recipients, were observed in the study. As expected, once-daily oxaprozin proved to be as effective as diclofenac three times daily in reducing the primary efficacy variable of patient-assessed shoulder pain score in patients with periarthritis of the shoulder refractory to previous treatments with other NSAIDs. Oxaprozin was shown to be superior to diclofenac in improving shoulder function and was considered by investigators and patients to have greater overall efficacy than diclofenac. In addition, oxaprozin showed a trend toward superior results in improving patients' quality of life compared with diclofenac. A trend towards better tolerability results for oxaprozin compared with diclofenac was also noted.

PMID:15324531 Heller B, Tarricone R; Curr Med Res Opin 20 (8): 1279-90 (2004)

/EXPL THER/: The effects of eye drops containing a propionic acid derivative (oxaprozin) at 0.1% concentration on ocular inflammation produced by sodium arachidonate in the rabbit's eye were evaluated. Furthermore, the aqueous bioavailability of the drug formulation in the uninflamed and inflamed eyes was evaluated. Oxaprozin eye drops significantly reduced the signs of ocular inflammation elicited by sodium arachidonate on conjunctiva and iris. Oxaprozin treatment significantly reduced the levels of polymorphonuclear leukocytes and protein concentration in aqueous samples obtained from the eyes treated with arachidonate. Present data suggest, for the first time, that oxaprozin may be employed topically to prevent ocular reactions where the arachidonic acid cascade is activated.

PMID:11858617 Bucolo C, Maltese A; J Ocul Pharmacol Ther 18 (1): 75-81 (2002)

4.3 Drug Warning

Clinical trials of several COX-2 selective and nonselective NSAIDs of up to three years duration have shown an increased risk of serious cardiovascular thrombotic events, myocardial infarction, and stroke, which can be fatal. All NSAIDs, both COX-2 selective and nonselective, may have a similar risk. Patients with known cardiovascular disease or risk factors for cardiovascular disease may be at greater risk. To minimize the potential risk for an adverse cardiovascular event in patients treated with a NSAID, the lowest effective dose should be used for the shortest duration possible. Physicians and patients should remain alert for the development of such events, even in the absence of previous cardiovascular symptoms. Patients should be informed about the signs and/or symptoms of serious cardiovascular events and the steps to take if they occur. /Nonsteroidal anti-inflammatory drugs/

Prescribing Information for Daypro (Oxaprozin); G.D. Searle LLC, Div. of Pfizer Inc, USA; (January 2007). Available from, as of February 12, 2008: https://media.pfizer.com/files/products/uspi_daypro.pdf

NSAIDs, including Daypro, can cause serious gastrointestinal (GI) adverse events including inflammation, bleeding, ulceration, and perforation of the stomach, small intestine, or large intestine, which can be fatal. These serious adverse events can occur at any time, with or without warning symptoms, in patients treated with NSAIDs. Only one in five patients, who develop a serious upper GI adverse event on NSAID therapy, is symptomatic. Upper GI ulcers, gross bleeding, or perforation caused by NSAIDs occur in approximately 1% of patients treated for 3-6 months, and in about 2-4% of patients treated for one year. These trends continue with longer duration of use, increasing the likelihood of developing a serious GI event at some time during the course of therapy. However, even short-term therapy is not without risk.

NSAIDs should be prescribed with extreme caution in those with a prior history of ulcer disease or gastrointestinal bleeding. Patients with a prior history of peptic ulcer disease and/or gastrointestinal bleeding who use NSAIDs have a greater than 10-fold increased risk for developing a GI bleed compared to patients treated with neither of these risk factors. Other factors that increase the risk of GI bleeding in patients treated with NSAIDs include concomitant use of oral corticosteroids or anticoagulants, longer duration of NSAID therapy, smoking, use of alcohol, older age, and poor general health status. Most spontaneous reports of fatal GI events are in elderly or debilitated patients and therefore, special care should be taken in treating this population. To minimize the potential risk for an adverse GI event in patients treated with an NSAID, the lowest effective dose should be used for the shortest possible duration. Patients and physicians should remain alert for signs and symptoms of GI ulcerations and bleeding during NSAID therapy and promptly initiate additional evaluation and treatment if a serious GI event is suspected. This should include discontinuation of the NSAID until a serious GI adverse event is ruled out. For high risk patients, alternate therapies that do not involve NSAIDs should be considered. /Nonsteroidal anti-inflammatory drugs/

As with other NSAIDs, anaphylactoid reactions may occur in patients without known prior exposure to Daypro. Daypro should not be given to patients with the aspirin triad. This symptom complex typically occurs in asthmatic patients who experience rhinitis with or without nasal polyps, or who exhibit severe, potentially fatal bronchospasm after taking aspirin or other NSAIDs

For more Drug Warnings (Complete) data for OXAPROZIN (18 total), please visit the HSDB record page.

4.4 Drug Indication

Used to relieve the inflammation, swelling, stiffness, and joint pain associated with rheumatoid arthritis and osteoarthritis.

FDA Label

5 Pharmacology and Biochemistry

5.1 Pharmacology

Oxaprozin is a nonsteroidal anti-inflammatory drug (NSAID) with analgesic and antipyretic properties. Oxaprozin is used to treat rheumatoid arthritis, osteoarthritis, dysmenorrhea, and to alleviate moderate pain.

5.2 MeSH Pharmacological Classification

Anti-Inflammatory Agents, Non-Steroidal

Anti-inflammatory agents that are non-steroidal in nature. In addition to anti-inflammatory actions, they have analgesic, antipyretic, and platelet-inhibitory actions. They act by blocking the synthesis of prostaglandins by inhibiting cyclooxygenase, which converts arachidonic acid to cyclic endoperoxides, precursors of prostaglandins. Inhibition of prostaglandin synthesis accounts for their analgesic, antipyretic, and platelet-inhibitory actions; other mechanisms may contribute to their anti-inflammatory effects. (See all compounds classified as Anti-Inflammatory Agents, Non-Steroidal.)

Cyclooxygenase Inhibitors

Compounds or agents that combine with cyclooxygenase (PROSTAGLANDIN-ENDOPEROXIDE SYNTHASES) and thereby prevent its substrate-enzyme combination with arachidonic acid and the formation of eicosanoids, prostaglandins, and thromboxanes. (See all compounds classified as Cyclooxygenase Inhibitors.)

5.3 FDA Pharmacological Classification

5.3.1 Active Moiety

OXAPROZIN

5.3.2 FDA UNII

MHJ80W9LRB

5.3.3 Pharmacological Classes

Cyclooxygenase Inhibitors [MoA]; Nonsteroidal Anti-inflammatory Drug [EPC]; Anti-Inflammatory Agents, Non-Steroidal [CS]

5.4 ATC Code

M - Musculo-skeletal system

M01 - Antiinflammatory and antirheumatic products

M01A - Antiinflammatory and antirheumatic products, non-steroids

M01AE - Propionic acid derivatives

M01AE12 - Oxaprozin

5.5 Absorption, Distribution and Excretion

Absorption

Oxaprozin is 95% absorbed after oral administration. Food may reduce the rate of absorption of oxaprozin, but the extent of absorption is unchanged. Antacids do not significantly affect the extent and rate of oxaprozin absorption.

Route of Elimination

Oxaprozin is expected to be excreted in human milk based on its physical-chemical properties; however, the amount of oxaprozin excreted in breast milk has not been evaluated. Approximately 95% of oxaprozin is metabolized by the liver. Approximately 5% of the oxaprozin dose is excreted unchanged in the urine. Sixty-five percent (65%) of the dose is excreted in the urine and 35% in the feces as metabolite. Biliary excretion of unchanged oxaprozin is a minor pathway. Several oxaprozin metabolites have been identified in human urine or feces.

Volume of Distribution

11 to 17 L/70 kg

In dose proportionality studies utilizing 600, 1200 and 1800 mg doses, the pharmacokinetics of oxaprozin in healthy subjects demonstrated nonlinear kinetics of both the total and unbound drug in opposite directions, i.e., dose exposure related increase in the clearance of total drug and decrease in the clearance of the unbound drug. Decreased clearance of the unbound drug was related predominantly to a decrease in the volume of distribution and not an increase in the half-life. This phenomenon is considered to have minimal impact on drug accumulation upon multiple dosing. The apparent volume of distribution (Vd/F) of total oxaprozin is approximately 11-17 L/70 kg. Oxaprozin is 99% bound to plasma proteins, primarily to albumin. At therapeutic drug concentrations, the plasma protein binding of oxaprozin is saturable, resulting in a higher proportion of the free drug as the total drug concentration is increased. With increases in single doses or following repetitive once-daily dosing, the apparent volume of distribution and clearance of total drug increased, while that of unbound drug decreased due to the effects of nonlinear protein binding. Oxaprozin penetrates into synovial tissues of rheumatoid arthritis patients with oxaprozin concentrations 2-fold and 3-fold greater than in plasma and synovial fluid, respectively. Oxaprozin is expected to be excreted in human milk based on its physical-chemical properties; however, the amount of oxaprozin excreted in breast milk has not been evaluated.

Daypro is 95% absorbed after oral administration. Food may reduce the rate of absorption of oxaprozin, but the extent of absorption is unchanged. Antacids do not significantly affect the extent and rate of Daypro absorption.

It is not known whether oxaprozin is distributed into human breast milk. However, it is distributed into the milk of lactating rats.

Thomson/Micromedex. Drug Information for the Health Care Professional. Volume 1, Greenwood Village, CO. 2007., p. 382

Approximately 5% of the oxaprozin dose is excreted unchanged in the urine. Sixty-five percent (65%) of the dose is excreted in the urine and 35% in the feces as metabolite. Biliary excretion of unchanged oxaprozin is a minor pathway, and enterohepatic recycling of oxaprozin is insignificant. Upon chronic dosing the accumulation half-life is approximately 22 hours. The elimination half-life is approximately twice the accumulation half-life due to increased binding and decreased clearance at lower concentrations.

For more Absorption, Distribution and Excretion (Complete) data for OXAPROZIN (8 total), please visit the HSDB record page.

5.6 Metabolism/Metabolites

Hepatic. Ester and ether glucuronide are the major conjugated metabolites of oxaprozin, and do not have significant pharmacologic activity.

Several oxaprozin metabolites have been identified in human urine or feces. Oxaprozin is primarily metabolized by the liver, by both microsomal oxidation (65%) and glucuronic acid conjugation (35%). Ester and ether glucuronide are the major conjugated metabolites of oxaprozin. On chronic dosing, metabolites do not accumulate in the plasma of patients with normal renal function. Concentrations of the metabolites in plasma are very low. Oxaprozin's metabolites do not have significant pharmacologic activity. The major ester and ether glucuronide conjugated metabolites have been evaluated along with oxaprozin in receptor binding studies and in vivo animal models and have demonstrated no activity. A small amount (<5%) of active phenolic metabolites are produced, but the contribution to overall activity is limited.

5.7 Biological Half-Life

54.9 hours

Upon chronic dosing the accumulation half-life is approximately 22 hours. The elimination half-life is approximately twice the accumulation half-life due to increased binding and decreased clearance at lower concentrations.

5.8 Mechanism of Action

Anti-inflammatory effects of Oxaprozin are believed to be due to inhibition of cylooxygenase in platelets which leads to the blockage of prostaglandin synthesis. Antipyretic effects may be due to action on the hypothalamus, resulting in an increased peripheral blood flow, vasodilation, and subsequent heat dissipation. Oxaprozin is a non-selective NSAID, with a cell assay system showing lower COX-2 selectivity implying higher COX-1 selectivity.

This study was undertaken to evaluate the scavenging activity for reactive oxygen species (ROS) and reactive nitrogen species (RNS) by several nonsteroidal anti-inflammatory drugs (NSAIDs), namely indole derivatives (indomethacin, acemetacin, etodolac), pyrrole derivatives (tolmetin and ketorolac), and an oxazole derivative (oxaprozin). The inhibition of prostaglandin synthesis constitutes the primary mechanism of the anti-inflammatory action of these drugs. Nevertheless, it has been suggested that the anti-inflammatory activity of NSAIDs may be also partly due to their ability to scavenge ROS and RNS and to inhibit the respiratory burst of neutrophils triggered by various activator agents. Thus, the scavenging activity of these NSAIDs was evaluated against an array of ROS (O(2)(-), HO, HOCl, and ROO) and RNS (NO and ONOO(-)) using noncellular in vitro systems. The results obtained demonstrated that tolmetin, ketorolac, and oxaprozin were not active against O(2)(-), while acemetacin, indomethacin, and etodolac exhibited concentration-dependent effects. Oxaprozin was also the least active scavenger for HO, among all the tested NSAIDs shown to be active. The scavenging effect for HOCl was not observed for any of the tested NSAIDs. The ROO was effectively scavenged by etodolac, with the other tested NSAIDs being much less active. NO and ONOO(-) were scavenged by all the tested NSAIDs.

PMID:15528048 Fernandes E et al; Free Radic Biol Med 37 (11): 1895-905 (2004)

Oxaprozin is a nonsteroidal anti-inflammatory drug characterised by a propionic acid-based structure. It is able to diffuse easily into inflamed synovial tissues after oral administration. Although discovered > 20 years ago, it is now under intensive investigation because of its unusual pharmacodynamic properties. Other than being a nonselective cyclooxygenase inhibitor, the drug is capable of inhibiting both anandamide hydrolase in neurons (median inhibitory concentration [IC50] = 85 umol/L), with consequent potent analgesic activity, and NF-kappaB activation in inflammatory cells (IC50 = 50 umol/L). Moreover, oxaprozin induces apoptosis of activated monocytes in a dose-dependent manner, with the effect being detectable at a concentration of 5 micromol/L and reaching the maximum activity at 50 umol/L. As monocyte-macrophages and NF-kappaB pathways are crucial for synthesis of proinflammatory and histotoxic mediators in inflamed joints, oxaprozin appears to be endowed with pharmacodynamic properties exceeding those presently assumed as markers of classical nonsteroidal anti-inflammatory drug.

PMID:15934904 Dallegri F et al; Expert Opin Pharmacother 6 (5): 777-85 (2005)

API SUPPLIERS

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USDMF

01

China Chemical Synthesis Industrial ...

China

Medlab Asia & Asia Health

Not Confirmed

02

Cilag Ag

Switzerland

Medlab Asia & Asia Health

Not Confirmed

03

Corden Pharma Bergamo Spa

Italy

Italy

Medlab Asia & Asia Health

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API Reference Price

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DOSAGE - TABLET;ORAL - 600MG

USFDA APPLICATION NUMBER - 18841

DOSAGE - CAPSULE;ORAL - 300MG

USFDA APPLICATION NUMBER - 217927

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